If you searched for Kennebunkport's Trail Fest this summer, you likely found a single line sitting at the top of the results: the Kennebunkport Conservation Trust made the decision to cancel its own signature race for 2026. For anyone who has laced up for it in past years, that reads like the end of something. It isn't. It's a handoff, and the fall trail calendar in the Kennebunks is actually busier than the old one-race tradition ever was.
The Trust's own notice is direct about why. Citing "the changing needs and capacity of our organization, volunteers, community partners, members and supporters," the Kennebunkport Conservation Trust said the race "no longer fits within our capabilities" and pointed people toward two other events happening this fall instead. That redirect is the part worth paying attention to, because it means the organization that has hosted this race for years isn't stepping away from trail running. It's stepping back from running the event itself while pointing to two others already filling the gap.
Three Races, One Trail System, Zero Overlap in Who's Behind Them
The race Kennebunkport residents knew as Trail Fest for years started and ended at KCT's own headquarters on Gravelly Brook Road, with a 5K, a 10K, and a half marathon winding through the Trust's preserves. That specific event is gone for 2026. But the Kennebunks haven't lost a fall trail race. They've picked up two.
The Arundel Conservation Trust runs its own Trail Fest, distinct from KCT's, now in its sixth year. It starts and finishes at the Arundel Municipal Building on Limerick Road, offers the same 5K, 10K, and half marathon distances, and adds a kids' bike race on what ACT describes as the first flow trail of its kind in Southern Maine, the Roll Um' Easy Bike Flow Trail. This is the event KCT's own cancellation notice names as one of the two it's steering people toward, which tells you the two trusts see their races as complementary rather than competing.
The second is new: a 25K called Bobcat Ridge, set for October 3 at KCT's Edwin L. Smith Preserve, the same preserve that hosted the old Trail Fest course. Registration is capped at 100 runners, and proceeds go to the Kennebunkport Conservation Trust, meaning KCT's own trail system is still the stage for a race this fall, just one it isn't organizing directly.
| Race | Organizer | 2026 Date | Location | Status |
|---|---|---|---|---|
| Trust Trail Fest | Kennebunkport Conservation Trust | — | KCT headquarters, 57 Gravelly Brook Road | Canceled for 2026 |
| ACT Trail Fest (6th Annual) | Arundel Conservation Trust | September 26 | Arundel Municipal Building, 257 Limerick Road | Running as scheduled |
| Bobcat Ridge 25K | Independent organizer, benefiting KCT | October 3 | Edwin L. Smith Preserve, Kennebunkport | New this year, capped at 100 runners |
| Holistic Hustle | Community fundraiser | October 31 | Emmons Preserve, Kennebunkport | Running as scheduled |
A third event rounds out the season without any connection to the cancellation at all. Holistic Hustle takes over Emmons Preserve on October 31 with a timed 5K, a trail 10K, and a kids' half-mile fun run, plus finisher medals and a raffle. It was already on the calendar before KCT made its call, which means the actual count of organized trail races in the Kennebunks this fall sits at three, not the zero that a quick glance at the cancellation notice might suggest.
What This Does to a Saturday in Late September
The timing compresses things. ACT's Trail Fest lands on September 26, the same Saturday the town's Fall Artisans Marketplace sets up at the Waterhouse Center with local makers and small businesses selling handmade goods and seasonal finds. Anyone planning that Saturday around one event should know the other is happening across town at the same time, not instead of it.
The Saturday morning Farmers Market on Garden Street runs through the same stretch, into November, so a runner finishing ACT's course has somewhere to go afterward that isn't just home. Kennebunk's HarvestFest typically follows in early-to-mid October. Last year's edition landed on October 18, with a craft fair, a costume parade, pumpkin decorating, and a scarecrow scavenger hunt through downtown. If this year's follows a similar pattern, it puts a second civic gathering on the calendar within roughly three weeks of the reshuffled trail races, and gives the season two distinct centers of gravity: one on the trails, one on Main Street.
October 31 stacks the most. Holistic Hustle's morning race at Emmons Preserve shares the date with downtown Kennebunk's evening Trick-or-Treat, where merchants along Summer Street hand out candy and the Waterhouse Center hosts a DJ and trick-or-treat trucks from 4 to 6 p.m. A runner finishing a 10K that morning could plausibly be back downtown in costume with their kids by late afternoon.
None of this is a coincidence born of poor planning. It's what happens when one organization steps back from an event it's run for years and two others, one long-standing and one brand new, absorb the space without needing to coordinate a shared calendar. The Kennebunks didn't lose a race. They gained a second organizer and a new one, and the closest thing to friction is a single overlapping Saturday between a trail race and an artisan market that most people can still work around.
Reading the Cancellation Correctly
The instinct to read "Trail Fest canceled" as "trail running canceled" is understandable, especially if the Kennebunkport Conservation Trust's version was the only one you'd ever run. But the Trust's own language points elsewhere on purpose. It named the two events replacing its slot in the calendar rather than leaving the space empty, and one of those replacements still finishes on KCT's own preserve and still funds KCT's work. The organization gave up running a race. It didn't give up the trail.
For anyone who lives near the Smith Preserve, the Arundel Community Trails, or Emmons Preserve, that distinction changes what the next six weeks look like. It's not one canceled tradition to mourn. It's three separate mornings on three different pieces of land, run by three different groups, each drawing its own crowd of runners, volunteers, and the friends and family who show up at the finish line with coffee.
If you're trying to plan around any of it, September 26 through October 31 is the window that matters most this year in the Kennebunks. Register early for Bobcat Ridge given its 100-runner cap, and check ACT's own event page before assuming the September 26 date holds, since race logistics can shift closer to the day.
If a fall Saturday in the Kennebunks leads you somewhere new this year, whether that's a preserve you haven't run before or a downtown block you usually skip, Brick & Barn Real Estate is always glad to talk about what else is worth knowing around here.